Piridicillin sodium, CL-867
4-硫化-1-氮基环[3.2.0]庚烷-2-羧酸,6-[[(2R)-2-[[[6-[4-[[双铯(2-羟基)氨基]磺酰]苯基]-1,2-二氢-2-羟基-3-吡啶基]氨基]-2-(4-羟基苯基)乙酰]氨基]-3,3-二甲基-7-氧基,钠盐(1:1),(2S,5R,6R)- 吡地西林 Chemical Name: (2S,5R,6R)-6-[2(R)-[6-[4-[N,N-Bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1,2-dihydropyridin-3-ylcarboxamido]-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt
CAS No. 69402-03-5, 69414-41-1 (free acid)
项目整合开发状态: Not Determined
项目研究机构:
合成路线:The reaction of sodium 4-acetylbenzenesulfonate (I) with SOCl2 in DMF gives 4-acetylbenzenesulfonyl chloride (II),which by condensation with diethanolamine (A) in water is convereted into 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide (III).The cyclization of (III) by treatment first with ethyl formate and sodium methoxide in THF and then with cyanoacetamide (B) in the same solvent yields 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinonitrile (IV),which is hydrolyzed with NaOH in water at 105 C in a pressure vessel to afford 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinic acid (V).The especification of (V) with N-hydroxysucinimide (VI) by means of dicyclohexylcarbodiimide (VI) in DMF gives the corresponding activated ester (VII).Finally this compound is condensed with amoxicillin (6-[1-amino-(4-hydroxyphenyl)acetylamino]penicillanic acid) (VIII) in dimethylacetamide.
📌 参考资料/链接：
参考文献标题:
文献作者:Kaltenbronn,J.S.; et al.
参考来源:BE 867778; DE 2824341; FR 2392999; JP 7916496; NL 7806038; US 4101661; US 4137408
📄 详细内容
合成路线:The reaction of sodium 4-acetylbenzenesulfonate (I) with SOCl2 in DMF gives 4-acetylbenzenesulfonyl chloride (II),which by condensation with diethanolamine (A) in water is convereted into 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide (III).The cyclization of (III) by treatment first with ethyl formate and sodium methoxide in THF and then with cyanoacetamide (B) in the same solvent yields 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinonitrile (IV),which is hydrolyzed with NaOH in water at 105 C in a pressure vessel to afford 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinic acid (V).The especification of (V) with N-hydroxysucinimide (VI) by means of dicyclohexylcarbodiimide (VI) in DMF gives the corresponding activated ester (VII).Finally this compound is condensed with amoxicillin (6-[1-amino-(4-hydroxyphenyl)acetylamino]penicillanic acid) (VIII) in dimethylacetamide.
参考文献标题:CI-867,a new broad-spectrum semisynthetic penicillin
文献作者:Kaltenbronn,J.S.; et al.
参考来源:J Antibiot 1979,32621-625
合成路线:The reaction of sodium 4-acetylbenzenesulfonate (I) with SOCl2 in DMF gives 4-acetylbenzenesulfonyl chloride (II),which by condensation with diethanolamine (A) in water is convereted into 4-acetyl-N,N-bis(2-hydroxyethyl)benzenesulfonamide (III).The cyclization of (III) by treatment first with ethyl formate and sodium methoxide in THF and then with cyanoacetamide (B) in the same solvent yields 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinonitrile (IV),which is hydrolyzed with NaOH in water at 105 C in a pressure vessel to afford 6-[4-bis(2-hydroxyethyl) aminosulfonylphenyl]-1,2-dihydro-2-oxonicotinic acid (V).The especification of (V) with N-hydroxysucinimide (VI) by means of dicyclohexylcarbodiimide (VI) in DMF gives the corresponding activated ester (VII).Finally this compound is condensed with amoxicillin (6-[1-amino-(4-hydroxyphenyl)acetylamino]penicillanic acid) (VIII) in dimethylacetamide.
参考文献标题:Piridicillin Sodium
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Sweetman,A.J.
参考来源:Drugs Fut 1980,5(4),195
产品链接: CAS No. 69402-03-5›› 产品链接: CAS No.69414-41-1››